ChemicalBook CAS DataBase List Efavirenz

Efavirenz synthesis

9synthesis methods

Product Name:Efavirenz
CAS Number:154598-52-4
Molecular formula:C14H9ClF3NO2
Molecular Weight:315.67

102-09-0 Synthesis

102-09-0
383 suppliers
$6.00/25g

209414-27-7 Synthesis

(S)-1-(2-Amino-5-chlorophenyl)-1-(trifluoromethyl)-3-cyclopropyl-2-propyn-1-ol

209414-27-7
126 suppliers
$55.00/10 mg

154598-52-4
482 suppliers
$25.00/1g

Yield:154598-52-4 98%

Reaction Conditions:

with 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran at 20 - 60; for 2 h;

Steps:

2
EXAMPLE-2 Preparation of Efavirenz From (S)-Amino Alcohol by Using Diphenylcarbonate: 1.5 g of (S)-amino alcohol (5.19 mmol) was dissolved in THF (20 ml) and DBU (1.7 ml, 11.42 mmol) was added at room temperature. Then diphenylcarbonate (4.443 g, 19.38 mmol) was added and the mixture was further stirred at 60° C. for 2h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was successively washed with aqueous hydrochloric acid, DM water and brine, concentrated and purified on silica gel column chromatography to get 90-98% yield of pure Efavirenz (HPLC purity=99.7%).

References:

LUPIN LIMITED US2012/108809, 2012, A1 Location in patent:Page/Page column 2-3